my views on two up might differ from others. for me, going two up means you need a bunch more power than most small bikes have to offer. also, your category of ADV to me means traveling multiple days self-sustained. that means a bunch of gear strapped on the back. Given those bits, I'd be opting for something at a 650cc minimum. perhaps a KLR might be enough, but more modern twins would be more powerful and capable. That would likely blow away your 350 pound max though.
I've been looking hard at a Himalayan, Honda CB500X, or KLR for doing ADV style riding. I've pretty much crossed off the Himi as it's not strong enough for highway use to get to destinations. the KLR is barely enough, but has better off-road characteristics than the CB500X. The 500X will be better on the highway with the twin cyl engine though. A nice used VStrom 650 might come into play though.
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